May 26, 2020 – Montreal mob associate Gregory (Picasso) Woolley was denied his request for parole and the opportunity to walk free more than a year early from a drug-dealing conviction because of the Coronavirus pandemic. Woolley was busted for possession of methamphetamine and marijuana inside the Montreal Detention Center two years ago.
The 48-year old Woolley is affiliated with both the Italian mafia and the Hells Angels biker gang in Quebec. He was arrested as part of a narcotics conspiracy case in 2015 and sentenced to eight years behind bars.
With his current sentence, he could still be released to a halfway house by December. Before his 2015 pinch, he had served two previous prison stints, one connected to a series of attempted murders tied to the Quebec Biker War.
In the 1990s, Woolley was close to notorious Hells Angel boss Maurice (Mom) Boucher and given leadership of a Hells Angel support club known as “The Rockers.” Woolley fought on the frontlines of the Quebec Biker War that engulfed the Canadian underworld between 1994 and 2002. The war pitted the Hells Angels against the Rock Machine and the Banditos for drug turf in Montreal. Today, Boucher is serving a life prison sentence for ordering the murders of two prison guards.
While in prison in the early 2000s, Woolley became close to vaunted Montreal mob don Vito Rizzuto. When Rizzuto’s mafia empire came under siege in 2009, Woolley brokered an alliance with the Hells Angels to aid the Rizzuto organization in fending off an insurrection. Rizzuto had helped mediate the end of the Quebec Biker War years earlier.
Rizzuto died of cancer in 2013 at 67 years old, allegedly turning over power in his crime family to his son, Leonardo. A police wiretapped conversation between Leonardo Rizzuto and Woolley in the summer of 2005, just weeks before Woolley was jailed, showed Rizzuto fawning over the influence Woolley wielded across multiple Montreal gangland factions.
Woolley is of Haitian descent. He headed the Master B crew, a Haitian street crew, as a teenager in the 1980s.
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